The research proposal that I have submitted is centered on the total synthesis of the enediyne antitumor antibiotic chromophore artifacts of maduropeptin. To date there has not been a total synthesis of the maduropeptin chromophore artifacts. Maduropeptin possesses potent antibiotic and antitumor properties and a manageable synthetic route will provide quantities of material for further biological testing as well as make the development of analogs possible. I will also present a series of maduropeptin analogs that may show increased biological activity and stability. A novel enediyne system will also be explored that may create a new subclass of enediyne antibiotics in the future.